Benzocaine → HCID 23457806, compound

HRID 126949Notes

Reaction equation

HRID 126949 reaction equation
O[CH:2]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH2:3][CH3:4].[CH2:17](N(CC)CC)C.CS(Cl)(=O)=O.[NH2:29][C:30]1[CH:40]=[CH:39][C:33]([C:34]([O:36][CH2:37][CH3:38])=[O:35])=[CH:32][CH:31]=1>CN(C)P(N(C)C)(N(C)C)=O.C(Cl)Cl>[CH2:3]([CH:2]([NH:29][C:30]1[CH:31]=[CH:32][C:33]([C:34]([O:36][CH2:37][CH3:38])=[O:35])=[CH:39][CH:40]=1)[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH3:4]

Participants

7

Reactant 4

HCID 2337BenzocaineHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 5477073-Pentadecanol

Product 1

HCID 23457806HCID 23457806, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 12679HexamethylphosphoramideSolvent

Procedure

Ten grams (43.8 m moles) 3-hydroxypentadecane and 4.9 g. (1.1 eq) triethylamine in 250 ml. methylene chloride is cooled to -10° C. in a dry ice-acetone bath. To the stirred solution is dropwise added 5.7 g. (1.1 eq) methanesulfonyl chloride in 10 ml. methylene chloride at a rate such that the reaction temperature does not exceed -5° C. After addition is complete, the solution is warmed to room temperature and washed in sequence with 100 ml. of the following ice-cold solutions: water, 10% hydrochloric acid, saturated sodium bicarbonate, and brine. The methylene chloride is dried and evaporated to a viscous, orange oil. Pentadecane-3-methanesulfonate (13.4 g. 43.7 m moles) and 14.4 g. (2 eq) ethyl 4-aminobenzoate in 75 ml. hexamethylphosphoramide is stirred at 120° C. for 18 hours. The cooled solution is diluted with 150 ml. water, the precipitate is filtered, washed with 150 ml. 50% aqueous ethanol and dried. Crystallization from ethanol and then from acetonitrile yields the product as a white solid.

Workup

  1. customdoes not exceed -5° C
  2. additionAfter addition
  3. washwashed in sequence with 100 ml
  4. dry with materialThe methylene chloride is dried
  5. customevaporated to a viscous, orange oil
  6. additionThe cooled solution is diluted with 150 ml
  7. filtrationwater, the precipitate is filtered
  8. washwashed with 150 ml
  9. dry with material50% aqueous ethanol and dried
  10. customCrystallization from ethanol

Sources & evidence

ORD record
ord-a30d415f621d43a2bd003e0e0bfd6b29
Source dataset
uspto-grants-1981_03
Patent number
US04254138

Reaction notes

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